Nimesh Gupta is the founder of Briefly, a legaltech generative AI company. I met Nimesh through a mutual friend, and we hit it off - our patent litigation background, views on parenting, therapy, and entrepreneurship. 

We take Nimesh’s unconventional moves from biglaw to big tech to startups and dig into the decisions. We explored how to assess risk and opportunities in new technologies and businesses, including legaltech and generative AI. Along the way we explore how mindfulness and authenticity provided a north star for career decisions.

Disclosure: I’m an advisor to Briefly.